Organic reactions in water: Highly rapid CAN mediated one-pot synthesis of nitriles from aldehydes under mild conditions

Synlett

Volumn , Issue 2, 2003, Pages 262-264

  Bandgar, B P ^a   Makone, S S ^a  

^a SWAMI RAMANAND TEERTH MARATHWADA UNIVERSITY   (India)

Author keywords

Aldehydes; Ceric ammonium nitrate (CAN); Nitriles; Organic reactions in water

Indexed keywords

ALDEHYDE; CERIUM NITRATE; NITRILE; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FILTRATION; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0037287086     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-36779     Document Type: Article

References (48)

1. (a) Mowry, D. T. Chem. Rev. 1948, 42, 250.
2. (b) Friedrich, K.; Wallensfels, K. In The Chemistry of the Cyano Group; Rappoport, Z., Ed.; Wiley-Intersicnece: New York, 1970.
3. (c) North, M. In Comprehensive Organic Functional Group Transformation; Katrizky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Pergamon: Oxford, 1995, 617-618.
4. (a) Findlay, J. A.; Tang, C. S. Can. J. Chem. 1967, 45, 1014.
5. (b) Forey, H. G.; Datlon, D. R. J. Chem. Soc., Chem. Commun. 1973, 628.
6. (c) Kukhar, V. P.; Fasternak, V. I. Synthesis 1974, 563.
7. (d) Shinozaki, H.; Imaizumi, M.; Tajima, M. Chem. Lett. 1983, 929.
8. (e) Meshram, H. M. Synthesis 1992, 943.
9. (f) Katritzky, A. R.; Zhang, G. F.; Fan, W. Q. Org. Prep. Proced. Int. 1993, 25, 315.
10. (g) Krause, J. G.; Shaikh, S. Synthesis 1974, 563.
11. (h) Flukuzaiwa, S.; Yamaishi, Y.; Funiya, H.; Terao, K.; Iwasaki, F. Tetrahedron Lett. 1997, 38, 7203.
12. (i) Villemin, D.; Lalaoui, M.; Ben Alloum, A. Chem. Ind. (London) 1991, 176.
13. (j) Rosini, G.; Baccolini, G.; Cacchi, S. J. Org. Chem. 1973, 38, 1060.
14. (k) Olah, G. A.; Narang, S. C.; Garcia-Luna, A. Synthesis 1980, 659.
15. (l) Olah, G. A.; Vankar, Y. D.; Garcia-Luna, A. Synthesis 1979, 227.
16. (a) Blatter, H. M.; Lukaszewski, H.; de Stevens, G. J. Am. Chem. Soc. 1961, 83, 2203.
17. (b) Olah, G. A.; Keumi, T. Synthesis 1979, 112; and references cited therein.
18. (c) Daunzonne, D.; Demerseman, P.; Royer, R. Synthesis 1981, 739.
19. (d) Saednya, A. Synthesis 1982, 190.
20. (e) Ganboa, I.; Palomo, C. Synth. Commun. 1983, 13, 219.
21. (f) Capeceivelle, P.; Lavigne, A.; Maumy, M. Synthesis 1989.
22. (g) Bose, D. S.; Narsaiah, A. V. Tetrahedron Lett. 1998, 39, 6533.
23. (h) Karmarkar, S. N.; Kelkar, S. L.; Wadia, M. S. Synthesis 1985, 510.
24. (i) Dauzonne, D.; Demergeman, P.; Royer, R. Synthesis 1981, 739.
25. (j) Dauzonne, D.; Demergeman, P.; Royer, R. Synthesis 1981, 739.
26. (k) Miller, M.; Loudon, G. J. Org. Chem. 1975, 40, 126.
27. (l) Fizet, C.; Streith, J. Org. Chem. 1975, 40, 126.
28. (m) Sosnovsky, G.; Krogh, J. A.; Umhoefer, S. G. Synthesis 1979, 722.
29. (n) Olah, G. A.; Keuni, T. Synthesis 1979, 112.
30. (a) Pomeroy, J. H.; Craig, C. A. J. Am. Chem. Soc. 1959, 81, 6340.
31. (b) Gela-Mialhe, Y.; Vessiere, R. Synthesis 1980, 1005.
32. (c) Furukawa, N.; Fukumura, M.; Akasaka, T.; Yoshimura, T.; Oac, S. Tetrahedron Lett. 1980, 21, 761,
33. (d) Georg, G. I.; Pfeifer, S. A. Tetrahedron Lett. 1985, 26, 2739,
34. (e) Nishiyama, K.; Oba, M.; Watanabe, A. Tetrahedron 1987, 43, 693.
35. (f) Suzuki, H.; Nakaya, C. Synthesis 1992, 641.
36. (a) Villemin, D.; Lalaoui, M.; Alloum, A. B. Chem. Ind. (London) 1991, 176.
37. (b) Delgado, E.; Cano, A. C.; Garcia, O.; Alvarado, J.; Velasco, L.; Alvarez, C.; Rudler, H. Synth. Commun. 1992, 2125.
38. (c) Feng, J. C.; Lin Ba, L.; Bian, N. S. Synth. Commun. 1998, 28, 3765.
39. (d) Das, B.; Madhusudhan, P.; Venkataiah, B. Synlett 1999, 1569.
40. Brackman, W.; Smit, P. J. Recl. Trev. Chim. 1963, 82. 757.
41. Parameswaran, K. N.; Friedman, O. M. Chem. Ind. (London) 1965, 988.
42. Misono, A.; Osa. T.; Koda, S. Bull. Chem. Soc. Jpn. 1966, 39, 854.
43. Sato, R.; Itoh, Y.; Itep, K.; Ni hina, H.; Goto, T.; Saito, M. Chem. Lett. 1984, 1913.
44. Okimoto, M.; Chiba, T. J. Org. Chem. 1978, 5, 218.
45. Erman, M. B.; Snow, J. W.; Williams, M. J. Tetrahedron Lett. 2000, 41, 6749.
46. Talukdar, S.; Hsu, J. L.; Chou, T. C.; Fang, J. M. Tetrahedron Lett. 2001, 42, 1103.
47. Roesky, H. W.; Mockel, K. Chemical Curiosities: VCH: Weinhein, 1996, 292-293.
48. 6N (257.24): C, 51.36; H, 5.88; N, 5, 45. Found: C, 51.41; H, 5.71; N, 5.49.